scholarly journals Chemical Constituents and an Antineuroinflammatory Lignan, Savinin from the Roots of Acanthopanax henryi

2019 ◽  
Vol 2019 ◽  
pp. 1-10 ◽  
Author(s):  
Xiao-Jun Li ◽  
Kwan-Woo Kim ◽  
Hyuncheol Oh ◽  
Xiang-Qian Liu ◽  
Youn-Chul Kim

The phytochemical investigation on the roots of Acanthopanax henryi (Araliaceae) resulted in the discovery of twenty compounds whose chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass spectrometry data, other physicochemical properties, and a comparison of the spectral data with the literature. They were identified as (-)-sesamin (1), helioxanthin (2), savinin (3), taiwanin C (4), 6-methoxy-7-hydroxycoumarin (5), behenic acid (6), 3-O-caffeoyl-quinic acid (7), 5-O-caffeoyl-quinic acid (8), 1,3-di-O-caffeoyl-quinic acid (9), 1,4-di-O-caffeoyl-quinic acid (10), 1,5-di-O-caffeoyl-quinic acid (11), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (12), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (13), ferulic acid (14), caffeic acid (15), stigmasterol (16), β-sitosterol (17), adenosine (18), syringin (19), and trans-coniferin (20). Among these isolates, compound 3 showed inhibitory activity against lipopolysaccharide- (LPS-) induced nitric oxide (NO) and prostaglandin E2 (PGE2) production with IC50 values of 2.22 ± 0.11 and 2.28 ± 0.23 μM, respectively. The effects of compound 3 were associated with the suppression of LPS-induced expression of the inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. Furthermore, compound 3 negatively regulated the production of interleukin- (IL-) 1β and tumor-necrosis factor- (TNF-) α at the transcriptional level in LPS-stimulated BV2 microglial cells. These antineuroinflammatory effects of compound 3 were mediated by p38 mitogen-activated protein kinase (MAPK).

2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.


2021 ◽  
Vol 21 (3) ◽  
pp. 699
Author(s):  
Sukee Sukdee ◽  
Puttinan Meepowpan ◽  
Narong Nantasaen ◽  
Siriporn Jungsuttiwong ◽  
Sarinya Hadsadee ◽  
...  

The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.


Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2455
Author(s):  
Xianwen Yang ◽  
Zhihui He ◽  
Yue Zheng ◽  
Ning Wang ◽  
Martin Mulinge ◽  
...  

Three new (1–3) and 25 known compounds were isolated from the crude extract of Cassia abbreviata. The chemical structures of new compounds were established by extensive spectroscopic analyses including 1D and 2D NMR and HRESIMS. Cassiabrevone (1) is the first heterodimer of guibourtinidol and planchol A. Compound 2 was a new chalcane, while 3 was a new naphthalene. Cassiabrevone (1), guibourtinidol-(4α→8)-epiafzelechin (4), taxifolin (8), oleanolic acid (17), piceatannol (22), and palmitic acid (28), exhibited potent anti-HIV-1 activity with IC50 values of 11.89 µM, 15.39 µM, 49.04 µM, 7.95 µM, 3.58 µM, and 15.97 µM, respectively.


2016 ◽  
Vol 54 (2) ◽  
pp. 214 ◽  
Author(s):  
Nguyen Manh Cuong ◽  
Pham Ngoc Khanh ◽  
Ho Viet Duc ◽  
Tran Thu Huong ◽  
Youn-Chui Kim ◽  
...  

Phytochemical investigation of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of 12 flavonoid and triterpenoid compounds,  including one new flavonoid, callistine A (1) and six known flavonoids 6,7- dimethyl-5,7-dihydroxy-4’-methoxy flavone (2), astragalin (3), quercetin (4), catechin (5), eucalyptin (6), and 8-demethyleucalyptin (7), along with 5 triterpenoids, 3-β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), betulinic acid (10), diospyrolide (11) and ursolic acid (12). Their chemical structures were determined from the spectroscopic evidences counting 1D- and 2D-NMR and HR-MS data. All the isolated compounds were examined for their anti-inflammatory activity against LPS-activated NO production in macrophage RAW264.7 cells. Among them, quercetin (4) and 3β-hydroxy-urs-11-en-13(28)-olide (9) showed potential inhibition activity in nitric oxide (NO)  production in RAW264.7 cells exposed to LPS.


2021 ◽  
Vol 59 (4) ◽  
pp. 498
Author(s):  
Nguyễn Quốc Vượng ◽  
Vu Van Chien ◽  
Nguyễn Thị Huế ◽  
Phạm Thị Hằng ◽  
Tran Van Hieu ◽  
...  

 From the roots of Myxopyrum smilacifolium Blume, five known compounds, verbascoside (1), arenarioside (2), myxopyroside (3), 3-formylindole (4), and 5-hydroxymethyl furfural (5) were isolated. Their chemical structures were determined by  ESI-MS, 1D, 2D-NMR spectrascopic data analysis as well as in comparison with those reported in the literatures.   


Marine Drugs ◽  
2018 ◽  
Vol 16 (7) ◽  
pp. 242 ◽  
Author(s):  
Paul Guillen ◽  
Sandra Gegunde ◽  
Karla Jaramillo ◽  
Amparo Alfonso ◽  
Kevin Calabro ◽  
...  

Two new zoanthamine alkaloids, namely 3-acetoxynorzoanthamine (1) and 3-acetoxyzoanthamine (2), have been isolated from the zoantharian Zoanthus cf. pulchellus collected off the coast of the Santa Elena Peninsula, Ecuador, together with three known derivatives: zoanthamine, norzoanthamine, and 3-hydroxynorzoanthamine. The chemical structures of 1 and 2 were determined by interpretation of their 1D and 2D NMR data and comparison with literature data. This is the first report of zoanthamine-type alkaloids from Zoanthus cf. pulchellus collected in the Tropical Eastern Pacific. The neuroinflammatory activity of all the isolated compounds was evaluated in microglia BV-2 cells and high inhibitory effects were observed in reactive oxygen species (ROS) and nitric oxide (NO) generation.


Holzforschung ◽  
2017 ◽  
Vol 71 (9) ◽  
pp. 697-703 ◽  
Author(s):  
Chuan-Ling Si ◽  
Yue Gao ◽  
Lei Wu ◽  
Rui Liu ◽  
Guanhua Wang ◽  
...  

Abstract Tree barks, residues in forestry and the pulp industry, could be a rich source of novel biologically or pharmaceutically active substances. In the current work, chemical constituents of extracts obtained from stem barks of Pinus massoniana have been analyzed. A novelty is the isolation of a new ursane-type triterpene saponin, which was characterized as ursolic acid 3-O-[β-d-glucopyranosyl (1′′→6′)]-β-d-glucopyranoside-28-O-β-d-glucopyranoside (IV). Moreover, three already known triterpenoid compounds ursolic acid (I), oleanolic acid (II) and oleanolic acid 3-O-β-d-glucopyranoside (III) are described. The elucidation of chemical structures of the isolated extractives was carried out mainly by a combination of 1D 1H, 13C and various 2D NMR experiments as well as by IR, UV and MS spectroscopic techniques. It is the first report about four triterpenoids found in bark of P. massoniana.


Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 573
Author(s):  
Chia-Chi Peng ◽  
Chiung-Yao Huang ◽  
Atallah F. Ahmed ◽  
Tsong-Long Hwang ◽  
Jyh-Horng Sheu

The present investigation on chemical constituents of the soft coral Sarcophyton cherbonnieri resulted in the isolation of seven new cembranoids, cherbonolides F–L (1–7). The chemical structures of 1–7 were determined by spectroscopic methods, including infrared, one- and two-dimensional (1D and 2D) NMR (COSY, HSQC, HMBC, and NOESY), MS experiments, and a chemical reduction of hydroperoxide by triphenylphosphine. The anti-inflammatory activities of 1–7 against neutrophil proinflammatory responses were evaluated by measuring their inhibitory ability toward N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced superoxide anion generation and elastase release in primary human neutrophils. The results showed that all isolates exhibited moderate activities, while cherbonolide G (2) and cherbonolide H (3) displayed a more active effect than others on the inhibition of elastase release (48.2% ± 6.2%) and superoxide anion generation (44.5% ± 4.6%) at 30 µM, respectively.


2019 ◽  
Vol 74 (10) ◽  
pp. 703-708 ◽  
Author(s):  
Georges Bellier Tabekoueng ◽  
Carine Mvot Akak ◽  
Moses K. Langat ◽  
Anatole Guy Blaise Azebaze ◽  
Alain François Kamdem Waffo ◽  
...  

AbstractThe phytochemical study of the roots, leaves and twigs of Penianthus camerounensis Dekker (Menispermaceae) has led to the isolation and the characterization of 20 compounds. A ceramide, camerounamide (1), and a furoclerodanediterpenoid, camerounin (2), have not been described previously, while the compounds xylopic acid (3), syringaresinol (4), iso-propylmethylcyclohexa-1,4-diol (5), 1-(28-hydroxyoctacosanoyl)glycerol (6), scoparone (7), friedelin (8), friedelanol (9) and betulinic acid (10) are being reported for the first time from the genus Penianthus alongside 10 known compounds (11–20). Chemical structures were determined using 1D- and 2D-NMR spectroscopy, MS and chemical analysis. Their chemotaxonomic importance is discussed.


2012 ◽  
Vol 67 (3-4) ◽  
pp. 144-150 ◽  
Author(s):  
Wafaa Hassan ◽  
Amal Gendy ◽  
Hanan Al-youssef ◽  
Assem El-Shazely

1A new eremophilane sesquiterpene, 1-β-hydroxy-8-oxoeremophila-7,9-dien-12-oic acid (), in addition to two known fl avonol glycosides, rutin (2) and quercetin-3-O-glucoside- 7-O-rutinoside (3), was isolated from the ethyl acetate fraction obtained from the aqueous alcoholic extract of the aerial parts of Senecio aegyptius var. discoideus Boiss. (family Asteraceae). The chemical structures of the isolated compounds were established by 1D and 2D NMR analysis (1H, 13C, COSY, HMQC, HMBC), MS and UV data, and through comparison with the literature. The ethyl acetate fraction and the isolated rutin showed significant cytotoxic activity against colorectal carcinoma (HCT 116) and to less extent against brain (U 251) and breast carcinoma (MCF 7). The ethyl acetate fraction showed a significant level of activity against Klebsiella pneumoniae, while the total extract showed the best antifungal activity against Candida albicans and Saccharomyces cerevisiae. DPPH radical scavenging activity of the ethyl acetate fraction was significant (96.7%) when compared to ascorbic acid. It also showed anti-inflammatory activity but no diuretic effect


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